He was elected a fellow of his college, and after taking orders became rector of Fladbury, Worcestershire, and chaplain to Richard Pate, sharing in his 1542 act of attainder.
On 12 August 1557 he was installed Dean of Worcester in the place of Philip Hawford, the last Abbot of Evesham, and about the same time he was instituted to the rectory of Bishop Cleeve, Gloucestershire.
Shortly before Mary's death, Cardinal Pole, then lying on his deathbed, sent Holland to the Princess Elizabeth, with a letter in which he dwelt on his fidelity, and begged her 'to give credit to whatever he shall say on my behalf'.
[3] As Holland refused to comply with the religious changes introduced after Elizabeth's accession, he was removed from the wardenship of All Souls, and in October 1559 he was deprived of the deanery of Worcester.
He was committed prisoner to the Marshalsea, and, dying in confinement, was buried on 6 March 1561 in St. George's parish, Southwark, brought to the church by about threescore gentlemen of the Inns of Court and Oxford.